Dimethylformamide → HCID 18929201, compound

Participants

Reaction Steps

A solution of 2-amino-6-chlorobenzoic acid (10 g, 0.06 mol), anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) was cooled to 0° C. in 300 mL 3-necked flask fitted with a magnetic stirrer and constant additional funnel. Bromoacetyl bromide was added dropwise over a 20-25 min period keeping the internal temperature between 0° to 1° C. After the addition was completed, the solution was allowed to warm to room temperature and stirring was continued for 20 h. The reaction mixture was cooled in an ice-bath and diluted with water (150 mL). The resulting yellow crystalline product was filtered, washed sequentially with 5% HBr solution (50 mL), water (50 mL), and then dried in vacuum oven (20 h, 40°-45° C.) to afford 5 g (30%) of the title compound, mp 133°-135° C. (decomp.); 1H NMR (CD3OD) 7.70 (d, 1H, J=8), 7.43 (t, 1H, J=8.4), 7.35 (d, 1H, J=8), 4.05 (s, 2H); 13C NMR (CD3OD) δ 168.19, 167.84, 137.24, 133.31, 132.85, 132.08, 128.78, 128.21, 124.20, 29.21; MS (EI, m/z) 293 (M+).

Provenance & Evidence